MDL-28170

CHEBI:82818 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A dipeptide resulting from the formal condensation of the carboxy group of N-benzyloxycarbonyl-L-valine with the amino group of L-phenylalanine aldehyde. It is a potent cell-permeable inhibitor of calpain I and II, and is also a γ-secretase inhibitor. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:140325 CHEBI:140325
CHEBI:17478 CHEBI:17478
CHEBI:23003 CHEBI:23003

Chemical structure

Computed structure properties
Molecular formula	C22H26N2O4
Charge	0
Average mass	382.46 Da
Monoisotopic mass	382.18926 Da
Source	ChEBI
InChIKey	NGBKFLTYGSREKK-PMACEKPBSA-N

SMILES

[H]C(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C

InChI

InChI=1S/C22H26N2O4/c1-16(2)20(24-22(27)28-15-18-11-7-4-8-12-18)21(26)23-19(14-25)13-17-9-5-3-6-10-17/h3-12,14,16,19-20H,13,15H2,1-2H3,(H,23,26)(H,24,27)/t19-,20-/m0/s1

Also called

benzyl [(2S)-3-methyl-1-oxo-1-{[(2S)-1-oxo-3-phenylpropan-2-yl]amino}butan-2-yl]carbamate (EXACT_SYNONYM)— chebi
Cbz-Val-Phe-H (EXACT_SYNONYM)— chebi
CbzValPheH (EXACT_SYNONYM)— chebi
L-benzyloxycarbonyl-L-valyl-L-phenylalaninal (EXACT_SYNONYM)— chebi
MDL 28,170 (EXACT_SYNONYM)— chebi
MDL 28170 (EXACT_SYNONYM)— chebi
MDL28170 (EXACT_SYNONYM)— chebi
N-CBZ-Val-Phe-al (EXACT_SYNONYM)— chebi
N-benzyloxycarbonyl-L-valyl-L-phenylalaninal (EXACT_SYNONYM)— chebi
N-benzyloxycarbonylvalylphenylalaninal (EXACT_SYNONYM)— chebi
N-benzyloxycarbonylvalylphenylalanine aldehyde (EXACT_SYNONYM)— chebi
Z-Val-Phe-CHO (EXACT_SYNONYM)— chebi
Z-Val-Phe-H (EXACT_SYNONYM)— chebi
Z-Val-Phe-al (EXACT_SYNONYM)— chebi
calpain inhibitor III (EXACT_SYNONYM)— chebi
carbobenzoxyvalylphenylalanine aldehyde (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:88191-84-8
lincs.smallmolecule:LSM-2958
reaxys:6824325

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:149553 CHEBI:149553
CHEBI:70868 CHEBI:70868

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:82818`	MDL-28170	`antibioticmech:chebi-d919fc43a4`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.